3-MCPD - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/3-MCPD

3-MCPD
From Wikipedia, the free encyclopedia

3-MCPD or (3-monochloropropane-1,2-diol or 3-chloro1,2-propanediol) is an organic chemical compound which is carcinogenic and highly suspected to be genotoxic in humans, has male anti-fertility effects, and is a chemical byproduct which may be formed in foods, the most commonly found member of chemical contaminants known as chloropropanols. It is primarily created in foods by protein hydrolysis by adding hydrochloric acid to speed up the reaction of the (soy) protein with lipids at high temperatures. Another method 3-MCPD can also occur in foods which have been in contact with materials containing epichlorohydrin-based wet-strength resins - used in the production of some tea bags and sausage casings.[1] It has been found in some East Asian and Southeast Asian sauces such as Oyster sauce, Hoisin sauce and Soy sauce.[2] Using hydrochloric acid rather than traditional slow fermentation is a far cheaper and faster method but unavoidably creates carcinogens.
CAS

3-MCPD

IUPAC name 3-chloropropane-1,2-diol Other names -Chlorohydrin, glycerol -monochlorohydrin, chlorodeoxyglycerol

Identifiers 96-24-2 7290

Contents
1 Absorption and toxicity 2 Legal limits 3 Incidents 4 Current status 5 See also 6 External links 7 References

number PubChem

ChemSpider 7018 EC number 202-492-4 KEGG ChEBI Jmol-3D images C18676 CHEBI:18721 Image 1 (http://chemapps.stolaf.edu /jmol/jmol.php?model=ClCC%28O%29CO) SMILES

Absorption and toxicity

3-MCPD is considered to be carcinogenic to rodents via a non-genotoxic mechanism[3]. It is able to cross the bloodtestis barrier and blood-brain barrier.[4] The oral LD50 of 3-chloro-1,2-propanediol was reported to be 152 mg/kg bodyweight in rats.[5] 3-MCPD also has male antifertility effects [6][7] and can be used as a rat chemosterilant[8].
Molecular C3H7ClO2 formula

InChI Properties

Molar mass 110.539 gmol1 Appearance Viscous, colorless liquid Density Melting point 1.32 gcm3 40 C, 233 K, -40 F

1 of 4

11/27/2011 8:14 AM

3-MCPD - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/3-MCPD

Legal limits
The joint Australia New Zealand Food Authority (ANZFA) set a limit for 3-MCPD in soy sauce of 0.02 milligrams per kilogram, in line with European Commission standards which came into force in the EU in April 2002.

Boiling point

213 C, 486 K, 415 F Hazards

MSDS R-phrases

External MSDS (http://msds.chem.ox.ac.uk /GL/glycerol_alpha_monochlorohydrin.html) R26/27/28, R36/37/38 S24, S45 (verify) (what is: / ?)

Incidents

S-phrases

A survey of soy sauces and similar products available in the Except where noted otherwise, data are given for materials UK was carried out by the Joint Ministry of Agriculture, in their standard state (at 25 C, 100 kPa) Fisheries and Food/Department of Health Food Safety and Infobox references Standards Group (JFSSG) in 2000 and reported more than half of the samples collected from retail outlets contained various levels of 3-MCPD [9]. In 2001 the United Kingdom Food Standards Agency found in tests of various oyster sauces and soy sauces that some 22% of samples contained a chemical called 3-MCPD (3-monochloropropane1,2-diol) at levels considerably higher than those deemed safe by the European Union. About two-thirds of these samples also contained a second chloropropanol called 1,3-DCP (1,3-dichloropropane-2-ol) which experts advise should not be present at any levels in food. Both chemicals have the potential to cause cancer and the Agency recommended that the affected products be withdrawn from shelves and avoided.[10][11] Britain's Food Standards Agency (FSA) singled out brands and products imported from Thailand, China, Hong Kong and Taiwan. Brands named in the British warning include Golden Mountain, King Imperial, Pearl River Bridge, Jammy Chai, Lee Kum Kee ( ), Golden Mark, Kimlan ( , Golden Swan, Sinsin, Tung Chun and Wanjasham soy sauce. Knorr soy sauce was also implicated, as well as Uni-President Enterprises Corporation ( ) creamy soy sauce from Taiwan, Silver Swan soy sauce from the Philippines, Ta Tun soy bean sauce from Taiwan, Tau Vi Yeu seasoning sauce and Soya bean sauce from Vietnam, Zu Miao Fo Shan soy superior sauce and Mushroom soy sauce from China and Golden Mountain and Lee Kum Kee chicken marinade.[12] Relatively high levels of 3-MCPD and other chloropropanols were found in soy sauce and other foods in China between 2002 and 2004[13]. In 2007 in Vietnam, 3-MCPD was found in toxic levels (Testing since 2001, In 2004, the HCM City Institute of Hygiene and Public Health found 33 of 41 sample of soya sauce with high rates of 3-MCPD, including six samples with up to 11,000 to 18,000 times more 3-MPCD than permitted, an increase over 23 to 5,644 times in 2001) [14] in soy sauces there in 2007, along with formaldehyde in the national dish Pho, and banned pesticides in vegetables and fruits. A prominent newspaper Thanh Nien Daily commented, "Health agencies have known that Vietnamese soy sauce, the country's second most popular sauce after fish sauce, has been chock full of cancer agents since at least 2001," [15] In March 2008 in Australia, "carcinogens" were found in soy sauces there, and Australians were advised to avoid soy sauce.[16] In Nov 2008, Britain's Food Standards Agency reported a wide range of household name food products from sliced bread to crackers, beefburgers and cheese with 3-MCPD above safe limits. Relatively high levels of the chemical were found in popular brands such as Mother's Pride, Jacobs

2 of 4

11/27/2011 8:14 AM

3-MCPD - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/3-MCPD

crackers, John West, Kraft Dairylea and McVitie's Krackawheat. The same study also found relatively high levels in a range of supermarket own-brands, including Tesco char-grilled beefburgers, Sainsbury's Hot 'n Spicy Chicken Drumsticks and digestive biscuits from Asda. The highest levels of 3-MCPD found in a non- soy sauce product, crackers, was 134 mcg per kg. The highest level of 3-MCPD found in soy sauce was 93,000 mcg per kg, 700 times higher. The legal limit for 3-MCPD coming in next year will be 20 mcg per kg. But the safety guideline on daily intake is 120mcg for a 60 kg person per day.[17]

Current status
These companies continue to use the rapid soy protein hydrolyzation method, but modify methods to lower contaminants to meet standards. Hydrolyzing always produces some 3-MCPD, but for the 1,3-DCP, a byproduct of 3-MCPD, there is no standard to meet as it is unregulated, scientists said that cancer found in reproductive cells caused by 1,3-DCP can cause cancer and genetic damage that can be passed to generations of offspring who have never been exposed to the chemical.[12]

See also
Food contamination

External links
Chloropropanols (WHO Food Additive Series 32) (http://www.inchem.org/documents/jecfa/jecmono /v32je17.htm)

References
1. ^ IFST issues statement on 3-MCPD (http://www.foodnavigator.com/Science-Nutrition/IFST-issues-statementon-3-MCPD) 2. ^ http://www.food.gov.uk/multimedia/webpage/soyproductsqa/ 3. ^ Robjohns S, Marshall R, Fellows M, Kowalczyk G (September 2003). "In vivo genotoxicity studies with 3-monochloropropan-1,2-diol" (http://mutage.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12960406) . Mutagenesis 18 (5): 4014. doi:10.1093/mutage/geg017 (http://dx.doi.org/10.1093%2Fmutage%2Fgeg017) . PMID 12960406 (http://www.ncbi.nlm.nih.gov/pubmed/12960406) . http://mutage.oxfordjournals.org /cgi/pmidlookup?view=long&pmid=12960406. 4. ^ Edwards et al. 1975 5. ^ Ericsson & Baker, 1970 6. ^ Ericsson RJ, Baker VF (March 1970). "Male antifertility compounds: biological properties of U-5897 and U-l5,646". Journal of reproduction and fertility 21 (2): 26773. doi:10.1530/jrf.0.0210267 (http://dx.doi.org /10.1530%2Fjrf.0.0210267) . PMID 5443210 (http://www.ncbi.nlm.nih.gov/pubmed/5443210) . 7. ^ Samojlik E, Chang MC (April 1970). "Antifertility activity of 3-chloro-1, 2-propanediol (U-5897) on male rats" (http://www.biolreprod.org/cgi/pmidlookup?view=long&pmid=5520328) . Biology of reproduction 2 (2): 299304. doi:10.1095/biolreprod2.2.299 (http://dx.doi.org/10.1095%2Fbiolreprod2.2.299) . PMID 5520328 (http://www.ncbi.nlm.nih.gov/pubmed/5520328) . http://www.biolreprod.org/cgi/pmidlookup?view=long& pmid=5520328. 8. ^ Ericsson RJ (July 1970). "Male antifertility compounds: U-5897 as a rat chemosterilant". Journal of reproduction and fertility 22 (2): 21322. doi:10.1530/jrf.0.0220213 (http://dx.doi.org/10.1530%2Fjrf.0.0220213) . PMID 5428943 (http://www.ncbi.nlm.nih.gov/pubmed/5428943) . 9. ^ Macarthur R, Crews C, Davies A, Brereton P, Hough P, Harvey D (November 2000). "3-monochloropropane1,2-diol (3-MCPD) in soy sauces and similar products available from retail outlets in the UK". Food additives and

3 of 4

11/27/2011 8:14 AM

3-MCPD - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/3-MCPD

10. 11. 12. 13.

14. 15. 16. 17.

contaminants 17 (11): 9036. doi:10.1080/026520300750038072 (http://dx.doi.org /10.1080%2F026520300750038072) . PMID 11271703 (http://www.ncbi.nlm.nih.gov/pubmed/11271703) . ^ Food.gov.uk press release soysauce (http://www.food.gov.uk/news/pressreleases/2001/jun/soysaucerecall) ^ Chart with five mentions of affected oyster sauces (http://www.food.gov.uk/multimedia/bigimages /soysauceproducts.gif) ^ a b barchronicle(Philippine government) (http://www.bar.gov.ph/barchronicle/2004/may04_1-31_soysauce.asp) ^ Fu WS, Zhao Y, Zhang G, et al. (August 2007). "Occurrence of chloropropanols in soy sauce and other foods in China between 2002 and 2004" (http://www.informaworld.com/openurl?genre=article&doi=10.1080 /02652030701246039&magic=pubmed) . Food additives and contaminants 24 (8): 8129. doi:10.1080/02652030701246039 (http://dx.doi.org/10.1080%2F02652030701246039) . PMID 17613068 (http://www.ncbi.nlm.nih.gov/pubmed/17613068) . http://www.informaworld.com/openurl?genre=article& doi=10.1080/02652030701246039&magic=pubmed. ^ Soya sauce stirs worry and discontentment among public (http://english.vietnamnet.vn/reports/2007/05/699774/) ^ Toxic soy sauce, chemical veggies -- food scares hit Vietnam (http://afp.google.com/article /ALeqM5iiMrrBvLTLGX3P0uXmSqeT1Zjayw) ^ 'Cancer chemical' in soy sauce (http://www.news.com.au/story/0,23599,23392636-29277,00.html) ^ The cancer chemical lurking in our food (http://www.dailymail.co.uk/health/article-61607/The-cancer-chemicallurking-food.html)

Retrieved from "http://en.wikipedia.org/w/index.php?title=3-MCPD&oldid=459759619" Categories: Organochlorides Carcinogens Diols This page was last modified on 9 November 2011 at 05:44. Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. See Terms of use for details. Wikipedia is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.

4 of 4

11/27/2011 8:14 AM